US6326504B1 - Procedure to extract natural products - Google Patents

Procedure to extract natural products Download PDF

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Publication number
US6326504B1
US6326504B1 US09/154,030 US15403098A US6326504B1 US 6326504 B1 US6326504 B1 US 6326504B1 US 15403098 A US15403098 A US 15403098A US 6326504 B1 US6326504 B1 US 6326504B1
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US
United States
Prior art keywords
solvent
extraction
supercritical fluid
vegetable
process according
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
US09/154,030
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English (en)
Inventor
Miguel Blasco Piquer
Bautista Enrique Mira Ferri
Juan Gabriel Martinez Fuentes
Gerardo Faus Fortea
Sebastian Subirats Huerta
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ASOCIACION DE INVETIGACION DEL LA INDUSTRIA AGROALIMENTARIA
Asociacion de Investigacion de la Industria Agroalimentaria AINIA
Original Assignee
Asociacion de Investigacion de la Industria Agroalimentaria AINIA
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Assigned to ASOCIACION DE INVETIGACION DEL LA INDUSTRIA AGROALIMENTARIA reassignment ASOCIACION DE INVETIGACION DEL LA INDUSTRIA AGROALIMENTARIA ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HUERTA, SEBASTIAN SUBIRATS, FERRI, BAUTISTA ENRIQUE MIRA, PIQUER, MIGUEL BLASCO, FORTEA, GERARDO FAUS, FUE, JUAN GABRIEL MARTINEZ
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/02Medicinal preparations containing materials or reaction products thereof with undetermined constitution from inanimate materials
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/12Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/56Materials from animals other than mammals
    • A61K35/60Fish, e.g. seahorses; Fish eggs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/185Magnoliopsida (dicotyledons)
    • A61K36/53Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/185Magnoliopsida (dicotyledons)
    • A61K36/75Rutaceae (Rue family)
    • A61K36/752Citrus, e.g. lime, orange or lemon
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/185Magnoliopsida (dicotyledons)
    • A61K36/87Vitaceae or Ampelidaceae (Vine or Grape family), e.g. wine grapes, muscadine or peppervine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/88Liliopsida (monocotyledons)
    • A61K36/906Zingiberaceae (Ginger family)
    • A61K36/9066Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D11/00Solvent extraction
    • B01D11/02Solvent extraction of solids
    • B01D11/0203Solvent extraction of solids with a supercritical fluid

Definitions

  • This invention relates to a procedure to extract organic products from vegetable or animal matrices, or their extracts, by means of high-pressure extraction using conventional liquid solvents and in the presence of small amounts of supercritical fluids.
  • the present invention relates to a high pressure process for extraction of organic products from vegetable or animal matrices or extracts thereof wherein the process is carried out in the presence of one or more liquid solvents and one or more supercritical fluids wherein the proportion of the supercritical fluid is less than 50% by weight of the total weight of the solvent and the supercritical fluid.
  • the process of the invention includes macerating the initial material at pressures of between 50 and 500 bar, in a solvent such as water, hydrocarbon, alcohol, ketone, ether, carbon halide or a mixture thereof, containing a supercritical fluid (SCF) such as CO 2 , propane, ethane or mixtures thereof in a proportion of less than 50% by weight of the total weight of the solvent and the SCF.
  • a supercritical fluid such as CO 2 , propane, ethane or mixtures thereof in a proportion of less than 50% by weight of the total weight of the solvent and the SCF.
  • the high working pressure causes the penetration of SCF, as it reduces its viscosity and increases diffusivity. This increase in diffusivity and reduction in viscosity causes the mobility of SCF through the inside of the cells and allows substances to be extracted at a much higher speed and in greater quantities than the conventional extractions or in other existing extraction patents to data.
  • the extraction mechanism means that the product extracted by the SCF is solvated quickly with traditional solvent, setting a balance between solute-SCF-conventional solvent which allows extraction to be performed at all times with the same levels of effectiveness and performance as at the start of the process. There is a continuous transfer of matter from the cells to the conventional solvent, using an intermediate phase formed by the SCF.
  • the innovation of the process over existing processes lies in the fact that proportions between SCF and conventional solvent are inverted, meaning that the resulting mixture is not an SCF but a pressure liquid or a mixture of phases.
  • This process means that the main solvent is not an SCF but ethanol, water or other solvents, which are found in greater proportions.
  • the SCF does not act as a solvent but as a transport vehicle between the vegetable matrix and the solvent.
  • the procedure according to the invention minimizes extraction time, reduces the solvent/solute ratio and therefore reduces pumping costs, the consumption of solvent and costs for its later recuperation.
  • the volume of the extractor is reduced for a certain production, or the production increases for a determined volume of extraction.
  • This type of extraction can be applied to the extraction of organic products such as essential oils, dyes, alkaloids, lipids, oils, waxes, proteins, fatty acids, aromas, spices, isoprenoids, steroids, carotenes, or active pharmaceutical principles present in, or originating from extracts provided by the technique, such as oleoresin or adsorbate, or present in or originating from biological matrices, such as orange skin, paprika, grape skin, coffee, tea, medicinal plants, seeds, carrot or fish viscera.
  • organic products such as essential oils, dyes, alkaloids, lipids, oils, waxes, proteins, fatty acids, aromas, spices, isoprenoids, steroids, carotenes, or active pharmaceutical principles present in, or originating from extracts provided by the technique, such as oleoresin or adsorbate, or present in or originating from biological matrices, such as orange skin, paprika, grape skin, coffee, tea, medicinal plants, seeds, carrot or fish viscera
  • the solvents that can be used in the process of the invention are those solvents that are conventionally used to extract organic products from vegetable or animal matrices or extracts thereof.
  • examples of such solvents include water, ethanol, and hexane.
  • Preferred solvents are pentane, hexane, dichlorfluoromethane, chlorofuluromethane, dichloromethane, dimethylethere, ethylmethylether, diethylether, methanol, ethanol, acetone, ethyl butyl ketone, or mixtures thereof.
  • Preferred SCF's include carbon dioxide, carbon anhydride, methane, ethane, propane, or mixtures thereof.
  • the proportion of SCF to solvent less than 50% by weight based on the total weight of the SCF and solvent.
  • the proportion of SCF to solvent is preferably between about 7 to about 35% by weight, most preferably about 11 to about 26 % by weight.
  • the higher concentrations of SCF are preferred when the animal or vegetable matrix is porous or akin.
  • the lower concentrations of SCF are preferred if the matrix is more compact and less porous.
  • the process according to the invention is performed at pressures of between 50 and 500 bar, preferably between about 150 to about 280 bar.
  • the time required to perform this operation is generally between about 0.25 and about 20 hours, preferably between about 0.5 and about 5 hours, most preferably between about 15 minutes and about 2 hours.
  • the extraction temperature is typically less than 90° C., preferably between about 40° C. and about 80° C.
  • the extracted product which is dissolved in the solvent is collected after depressurization.
  • This technique can be combined with a separation phase which allows the extract to be recuperated or fractionated.
  • This recuperation or fiactionation can be carried out following any process offered by the technique and known in the prior art.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Medical Informatics (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Botany (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Cell Biology (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Developmental Biology & Embryology (AREA)
  • Immunology (AREA)
  • Virology (AREA)
  • Zoology (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Medicines Containing Plant Substances (AREA)
US09/154,030 1997-01-28 1998-09-16 Procedure to extract natural products Expired - Fee Related US6326504B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/ES1997/000015 WO1998032449A1 (es) 1996-02-22 1997-01-28 Procedimiento para extraer productos naturales mediante fluidos supercriticos

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/ES1997/000015 Continuation-In-Part WO1998032449A1 (es) 1996-02-22 1997-01-28 Procedimiento para extraer productos naturales mediante fluidos supercriticos

Publications (1)

Publication Number Publication Date
US6326504B1 true US6326504B1 (en) 2001-12-04

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US09/154,030 Expired - Fee Related US6326504B1 (en) 1997-01-28 1998-09-16 Procedure to extract natural products

Country Status (6)

Country Link
US (1) US6326504B1 (es)
EP (1) EP0917876B1 (es)
AT (1) ATE285242T1 (es)
CA (1) CA2250051A1 (es)
DE (1) DE69732031D1 (es)
WO (1) WO1998032449A1 (es)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030099565A1 (en) * 2001-10-12 2003-05-29 Korea Institute Of Science And Technology Method for removing waxes from molded part in powder injection molding by using mixed fluid
US6576273B2 (en) * 2000-08-24 2003-06-10 Chr. Hansen A/S Purification process for improving total yield of curcuminoid colouring agent
US20040026318A1 (en) * 2000-06-22 2004-02-12 Lemaire Benoit Method for fractionating essential oils using at least a fluorinated solvent
US20040131748A1 (en) * 2002-11-12 2004-07-08 Water Solutions, Inc. Process for extracting carotenoids from fruit and vegetable processing waste
US20040191384A1 (en) * 2003-03-25 2004-09-30 Naik Jarpla Pura Process for the preparation of colorant from oleoresin
US20060213533A1 (en) * 1997-12-24 2006-09-28 Imam Emami Use of polyphenol compounds or derivatives thereof as free-radical scavengers in cigarette filters
US20060252949A1 (en) * 2003-09-25 2006-11-09 Lalit Chordia Recovery of residual specialty oil
FR2905284A1 (fr) * 2006-08-29 2008-03-07 Nat Invo Sarl Procede d'extraction d'une substance d'un materiau.
US20080233238A1 (en) * 2007-02-08 2008-09-25 Grimmway Enterprises, Inc. Supercritical co2 carrot feedstock extraction
EP1986756A1 (en) * 2006-02-07 2008-11-05 Industrial Research Limited Near-critical fluid extraction process
US20110094961A1 (en) * 2009-10-22 2011-04-28 Epic Oil Extractors, Llc Extraction of solute from solute-bearing material
US20110112329A1 (en) * 2009-11-11 2011-05-12 Dynasep Llc Energy efficient acetone drying method
EP2428258A1 (en) * 2010-05-31 2012-03-14 China Agricultural University Process for extracting plant-derived natural products with polarity or intermediate polarity
US9132363B2 (en) 2012-11-20 2015-09-15 Apeks Llc Extraction system
US9908062B2 (en) 2012-11-20 2018-03-06 Andrew Paul Joseph Extraction apparatus and method
CN108288738A (zh) * 2018-01-30 2018-07-17 常州大学 一种采用超临界二氧化碳流体回收锂离子电池电解液的方法

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITAN20030053A1 (it) * 2003-10-08 2005-04-09 Mauro Angeletti Processo per la produzione di estratto da semi d'uva a basso contenuto di polifenoli monomerici
BRPI0709379A2 (pt) * 2006-03-17 2011-07-12 Herbalscience Singapore Pte Ltd extratos e métodos que compreendem espécies de cúrcuma
CZ301511B6 (cs) * 2008-06-25 2010-03-31 Ceská geologická služba Metoda na získávání vápnitých nebo pyritizovaných fosílií z vápnitých hornin
CN112843776A (zh) * 2020-12-24 2021-05-28 常州市芙丽佳生物科技有限公司 一种橄榄仁提取物的提纯工艺

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5110509A (en) 1988-07-25 1992-05-05 Siegfried K. Peter Process for the recovery of monoglycerides and diglycerides from a mixture containing monoglycerides, diglycerides, and triglycerides
US5210240A (en) * 1984-08-09 1993-05-11 Siegfried Peter Process for the extraction of oil containing vegetable materials

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD294280A5 (de) * 1990-05-11 1991-09-26 Adw Institut Fuer Biotechnologie,De Verfahren zur gewinnung von polyhydroxyfettsaeuren aus bakterienbiomasse

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5210240A (en) * 1984-08-09 1993-05-11 Siegfried Peter Process for the extraction of oil containing vegetable materials
US5110509A (en) 1988-07-25 1992-05-05 Siegfried K. Peter Process for the recovery of monoglycerides and diglycerides from a mixture containing monoglycerides, diglycerides, and triglycerides

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8567412B2 (en) 1997-12-24 2013-10-29 Biosyntec Use of polyphenol compounds or derivatives thereof as free-radical scavengers in cigarette filters
US20060213533A1 (en) * 1997-12-24 2006-09-28 Imam Emami Use of polyphenol compounds or derivatives thereof as free-radical scavengers in cigarette filters
US20040026318A1 (en) * 2000-06-22 2004-02-12 Lemaire Benoit Method for fractionating essential oils using at least a fluorinated solvent
US6942881B2 (en) 2000-08-24 2005-09-13 Chr. Hansen A/S Purification process for improving total yield of curcuminoid coloring agent
US20030180401A1 (en) * 2000-08-24 2003-09-25 Chr. Hansen A/S Purification process for improving total yield of curcuminoid colouring agent
US6576273B2 (en) * 2000-08-24 2003-06-10 Chr. Hansen A/S Purification process for improving total yield of curcuminoid colouring agent
US20030099565A1 (en) * 2001-10-12 2003-05-29 Korea Institute Of Science And Technology Method for removing waxes from molded part in powder injection molding by using mixed fluid
US20040131748A1 (en) * 2002-11-12 2004-07-08 Water Solutions, Inc. Process for extracting carotenoids from fruit and vegetable processing waste
US7138152B2 (en) 2002-11-12 2006-11-21 Water Solutions, Inc. Process for extracting carotenoids from fruit and vegetable processing waste
US20070071861A1 (en) * 2002-11-12 2007-03-29 Water Solutions, Inc. Process for extracting carotenoids from fruit and vegetable processing waste
US7527820B2 (en) 2002-11-12 2009-05-05 Water Solutions, Inc. Composition resulting from process for extracting carotenoids from fruit and vegetable processing waste
US20040191384A1 (en) * 2003-03-25 2004-09-30 Naik Jarpla Pura Process for the preparation of colorant from oleoresin
US7501141B2 (en) * 2003-03-25 2009-03-10 Council Of Scientific And Industrial Research Process for the preparation of colorant from oleoresin
US20060252949A1 (en) * 2003-09-25 2006-11-09 Lalit Chordia Recovery of residual specialty oil
EP1986756A1 (en) * 2006-02-07 2008-11-05 Industrial Research Limited Near-critical fluid extraction process
US20100151098A1 (en) * 2006-02-07 2010-06-17 Industrial Research Limited Near-critical fluid extraction process
EP1986756A4 (en) * 2006-02-07 2010-07-21 Ind Res Ltd PROCESS FOR EXTRACTION WITH NEARLY CRITICAL FLUID
US8580116B2 (en) 2006-02-07 2013-11-12 Industrial Research Limited Near-critical fluid extraction process
FR2905284A1 (fr) * 2006-08-29 2008-03-07 Nat Invo Sarl Procede d'extraction d'une substance d'un materiau.
US20080233238A1 (en) * 2007-02-08 2008-09-25 Grimmway Enterprises, Inc. Supercritical co2 carrot feedstock extraction
US8398857B2 (en) 2009-10-22 2013-03-19 Epic Oil Extractors, Llc Extraction of solute from solute-bearing material
US20110094961A1 (en) * 2009-10-22 2011-04-28 Epic Oil Extractors, Llc Extraction of solute from solute-bearing material
WO2011060170A1 (en) * 2009-11-11 2011-05-19 Dynasep Llc Energy efficient acetone drying method
US8415506B2 (en) 2009-11-11 2013-04-09 Dynasep Inc. Energy efficient acetone drying method
US20110112329A1 (en) * 2009-11-11 2011-05-12 Dynasep Llc Energy efficient acetone drying method
EP2428258A1 (en) * 2010-05-31 2012-03-14 China Agricultural University Process for extracting plant-derived natural products with polarity or intermediate polarity
EP2428258B1 (en) * 2010-05-31 2017-03-29 China Agricultural University Process for extracting plant-derived natural products with polarity or intermediate polarity
US9132363B2 (en) 2012-11-20 2015-09-15 Apeks Llc Extraction system
US9908062B2 (en) 2012-11-20 2018-03-06 Andrew Paul Joseph Extraction apparatus and method
US9908063B2 (en) 2012-11-20 2018-03-06 Andrew Paul Joseph Extraction apparatus
CN108288738A (zh) * 2018-01-30 2018-07-17 常州大学 一种采用超临界二氧化碳流体回收锂离子电池电解液的方法
CN108288738B (zh) * 2018-01-30 2021-03-23 常州大学 一种采用超临界二氧化碳流体回收锂离子电池电解液的方法

Also Published As

Publication number Publication date
CA2250051A1 (en) 1998-07-30
ATE285242T1 (de) 2005-01-15
EP0917876A1 (en) 1999-05-26
DE69732031D1 (de) 2005-01-27
EP0917876B1 (en) 2004-12-22
WO1998032449A1 (es) 1998-07-30

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